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4000 sq. ft. NEW for stays March 1, 2026 and after, golf cart included with your stay!** Take a CHILL PILL: sleeps 24 in beds - max 12 adults. Only 12 & under in bunks. 6 King suites and 12 twins (8 in huge bunk room also with private bath).
LOCATION: Chill Pill is the directly across the street from the beach with a perfect location and has an amazing layout and extensive beach supplies provided. Short 150 steps to the beach access, views from 2nd & 3rd floors, walking distance to dozens of restaurants/activities including 85+ restaurants/stores at Destin Commons, also Whole Foods and Publix about a half-mile away.
+ SHUFFLEBOARD/ POOL tables, quality time with family/friends!
+SLEEPING: 6 King bedrooms ALL with private bathroom attached, plus 500 sq ft BUNKROOM with 4 sets built-in twin bunks - 7.5 bathrooms.
+WHAT WE PROVIDE (BEACH SUPPLIES):
-- 6 PAID beach chairs/umbrella set-up (3 double set-ups professional chair service) at end of the beach access at Hutchinson Street. *SEASONAL March-October*
-- Stand up paddleboard (SUP) AND sea kayak
-- 6 more fold-up sand chairs
-- a rolling beach cart and two rolling coolers, various floats and sand toys
-- appx 12 beach towels
+ELECTRONICS: EVERY bedroom has its own 4K wi-fi Amazon Firestick TV; SONOS speakers on main floor, stream wirelessly or connect with Aux cord.
+PRIVATE POOL with tanning shelf: Two sets French doors open to PRIVATE +POOL (15 X 25) . Adirondacks and gas grill by pool. Pool heat is seasonal at owner discretion and billed for full stay by a few days in advance, by Stripe invoice. Usually Oct - April/May
+LOUNGE/LIVING areas: Massive 43' X 17' living room split down the middle with two high-top gathering tables which seat 20 + 4 barstools at 9X5 kitchen island; one end has a Presidential pool table and shuffleboard table; the other end has three leather couches; both ends have 65" 4K Amazon Firestick wi-fi TVs wall-mounted. SONOS wi-fi speakers with paid Pandora & Spotify accounts.
+BATHROOOMS: (7.5 baths) are walk-in tiled showers except the 2 "family" bedrooms which have King PLUS a set of twin bunks and have a tub/shower combo to bathe any little ones
+KITCHEN: has all the gadgets including trash compactor, built-in ice maker under counter, Keurig plus drip brew station, TWO refrigerators (one in laundry), even basic spices are included; 5-burner gas cooktop, DOUBLE OVEN, and pot filler
+BUNK ROOM entire 3rd floor is 34' X 15' with loft ceilings and houses 4 sets of sturdy, built-in twin bunks (8 twins) and has its own LOUNGE AREA with 3 more leather couches, and large 65" 4K wi-fi TV.
+High-end mattresses and 650-thread count linens; clean-lines coverlets, wood-look tile and LVP flooring is cleaner than carpets; minimal area rugs, lots of original artwork from local artists complement the fun, coastal vibe of this house.
+BEDDING, no sleeper sofas: 6 Masters: 6 Kings, 2 sets twin bunks in the 2 family King rooms; plus bunk room with (4) sets of BUILT-IN twin bunks. TOTAL 24 in beds; max of 12 adults
+PARKING for MAX 6 vehicles (per city of Destin) but if you have SUVs or trucks, plan on only 5. NO RVs, trailers, boats or jet skis, NO street parking and no parking across sidewalk.
Unique Benefits
Free chair service for 6 (seasonal March thru October). Golf cart included with stays as of March 1, 2026. No wasted space, no sharing bathrooms, pool table AND shuffleboard table for loads of fun with family & friends, private pool - plus TONS of beach supplies provided like a stand-up-paddleboard, kayak, and many other items!
Why Kids Love It
Kids have their own "crow's nest," top floor 500-sq ft bunk room with 8 built-in twins, its own lounge area with 3 leather couches, 65" TV, and views of the beach. Private pool is easy to heat from our phone app, in cooler weather.
Crystal Shores is a beautiful neighborhood. Step out our pool gate and you're just 150 steps to the beach access. There is a restaurant on each side of us about a half of a block, plus dozens of restaurants, activities, movies, bowling, grocery stores, etc. all within walking distance. We are 6/10ths of a mile to the Destin Commons with 85+ stores and restaurants: Movie theater, Uncle Bucks, Bass Pro Shop, Build-a-Bear, Forever 21, etc.
Uncle Bucks for bowling, Destin Commons with shops and restaurants, movie theater, Bass Pro Shop, dozens of restaurants and stores.
LOCAL info will be provided by email with info on Crab Island, other activities and local restaurants and tips.
LOCAL info will be provided by email with info on Crab Island, other activities and local restaurants and tips.
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| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
Dec 01 - Dec 17 2025 | $499 | $549 | $3,750 | 3 nights | |
Dec 18 - Dec 22 2025 | $775 | 3 nights | |||
Dec 23 - Dec 27 2025 | $900 | 4 nights | |||
Dec 28 2025 - Jan 01 2026 | $1,000 | 4 nights | |||
Jan 02 - Jan 08 2026 | $699 | $900 | 4 nights |
Fees:
Notes:
-- MAX 12 adults, no exceptions. Only 12 & under in bunks.
--NO SMOKING - NO PETS.
--Partial down payment to book; balance due 60 days prior to arrival unless booked on short notice.
--An additional but REFUNDABLE security deposit of $500 is required.
--Minimum age limit to rent is 27. Any non-familial, all-adult groups must ALL be 27 years old, not just the booking person.
--No Spring Breakers/College break groups/Bachelor-Bachelorette parties, and no events (families only)
--PARKING for 6 vehicles per City of Destin, NO STREET PARKING
Last updated on November 23, 2025
Carrie S.Amazing!
This house had it all!!! It was perfect for our group of 20. The kids loved having their own space on the third floor, the parents enjoyed the king suites! The location, the pool, the beautiful house, all the extras (beach towels,beach chairs, beach wagon etc.) the chair set up a the beach all much appreciated! The entire process was seamless, great communication with owners and had no issues. Will definitely be back!
Stayed: August 2025 Submitted: August 13, 2025
Host response
"Thrills my soul, Carrie and the Gang! Exactly why we designed this house as a place everyone could gather and not feel crowded, especially with not sharing bathrooms! Hope memories were made and we welcome you back anytime! Thanks for your kind words - Dana"
Laura J.Perfect Family Vacation
We booked a family vacation (3 generations!) at TJ & Dana's Chill Pill house. The house is spectacular! And huge! Everyone had a king sized bed and their own bathroom. So luxurious. We didn't spend a ton of time at the beach (just daily morning walks and 1 afternoon) because the house had everything we needed. We so much enjoyed the private pool and playing pool & shuffleboard! The house was equipped with everything we could have needed (including a pack & play for my grandson!) The location was great - 1 block from the beach... and we were so close to grocery stores, restaurants, and other fun activities. It was exactly the kind of vacation I wanted for our family - fun & relaxing & beyond comfortable! We already want to come back!!!
Stayed: November 2023 Submitted: November 12, 2023
Laurie S.Just perfect for our large group!
We loved our week at the Chill Pill! Everything was exactly as described, and as others have said in past reviews, if we had a couple small things, they were addressed immediately. We were literally a few steps away from the most beautiful beach, with our chairs set up for us daily, what a great touch so we didn't have to rush down there in the mornings!!! We had some bad weather that kept us indoors a couple of days, but the shuffleboard and pool table were the perfect added amenity. We used that in the evenings, when it was raining, etc! They even had board games etc in a cabinet that we were able to play! Really, every detail was thought of, and our group of 13 had more than enough room. We didn't use the bunkroom as much as we expected due to our group being smaller than originally planned, but that was a huge space for kids sleeping and having a place to hang out away from the rest of the house. Just a perfect stay, and we hope to go back!! Thank you, Dana and TJ!
Stayed: October 2023 Submitted: November 06, 2023
Carla J.Perfect for large families or groups
We vacationed with my husband's whole family, 8 adults and 6 kids in all. We had PLENTY of space to hang out and be together as a family, and we could also enjoy a bit of quiet time when needed. We loved that the house had a shuffleboard table and beach service. I didn't realize how helpful beach service truly is. No one had to wake up early and claim our spot on the beach. The house is beautiful and was perfect for us. Dana was super responsive and helpful when contacted. I would definitely consider staying either at this or another of their properties again in the future.
Stayed: August 2023 Submitted: August 16, 2023
Julie H.Perfect, perfect vacation!!!
Chill Pill was the absolute perfect stay for our group of 21. My husband and I were joined by our five children and their families… 11 adults and 10 children ( 1 spouse couldn’t attend). The house was set up ideally for the grownups and kiddos to have their own spaces … bunk room for 8 with lounge area and bath… 6 bedrooms with en suite baths! The house is beautiful and had everything we needed… loved the kichen and downstairs “fun” area with shuffleboard and pool table and the outside pool. Close, safe walk to the beach and great to have beach chairs and umbrellas ready for us each day! Hosts thought of everything and made our vacation one of our best ever! Will be back! ️
Stayed: August 2023 Submitted: August 12, 2023
Timmy L.Blue Barracuda THE BEST
Blue Barracuda was the BEST. It was very spacious, even with our party of 20! With the multiple living areas, everybody could make themselves comfortable without feeling crowded, even with the unfortunate weather that we had all week. The kitchen had everything you could possibly need and so did the rest of the house! And last but not least, the backyard…..IT WAS AMAZING! The pool & hot tub were on a grand scale which matched the house perfectly; everything you could possibly need! We will be back to the Blue Barracuda next year!! Thank you so much Dana & TJ, y’all are the best hosts!
Stayed: July 2023 Submitted: July 20, 2023
Johnny P.Fantastic for large Groups
Wow! What a fabulous vacation. It will be hard to recreate this experience. If found the home to be so much more than a home you rented. There were so many things in the home and the additional amenities that were so thoughtful of your guests. And I did feel like your guests, not only a renter. My family of 5 opts for vacation home rental rather than hotel stays fairly often since 5 big people do not easily fit on 2 hotel beds. So we have stayed in enough of them for me to say this experience stood out. This is an exceptional home. I had made a contingency plan to buy whatever kitchen items we needed to cook for the whole party of 15. The Chill Pill kitchen had everything we needed and more. Two crockpots were so great. We used the 4 slice toaster everyday. Plenty of large skillets. More than enough dishes, bowls, mugs and other cups. The second floor was so cool to me. I couldn't believe when the listing said 6 king suites. But it was all there and not cramped. Not even the hallway was small. I found the care for the guest in the home even in the way in was constructed. There's so much to be thankful for, but the last thing I will mentioned is the paid for setups at the beach along with the additional supplies in the storage shed. You could have done so much less, but these touches really elevated my family's week together in Destin. It is so appreciated. We all needed a vacation, but my parents really needed all of their daughters and grandkids together without bitterness or bickering. Your hospitality was part of shutting all of that out. Thank you again. ️from Laura on behalf of Prewitt party of 15
Stayed: July 2023 Submitted: July 17, 2023
PJ S.Repeat Visitor
This was our group's second stay at the Chill Pill in Destin. This is the best house and best owners we have ever rented from...and we travel quite a bit. Every detail was thought out when building this home. Great hang out area w/ the shuffleboard and pool tables, 2 TVs, amazing bunk room, 5 seconds from the beach, etc. We will be back!
Stayed: March 2023 Submitted: March 29, 2023
Scott G.Great Property, Great Location!!
“Chill Pill” property by Dana, Destin Florida. What a great property for a large group or family! Steps from the beach. We stayed 3/4 - 3/11/23. All the amenities you could imagine! Two washers and dryers! That was hugh! A trash compactor, ice machine, two refrigerators, pool table, shuffle board, three umbrellas and six chairs set up daily for you at the beach, to name a few. All of the beach toys, from toddlers all the way up to adults with paddle board, kayak etc, etc. Many more beach chairs too! This property has it all! The heated pool was great and the young ones definitely enjoyed the warmth! Each bedroom has a full bath with King beds! Dana, the property manager was awesome, from beginning to end! Never too much trouble to answer any questions or provide personal feedback on local businesses! This was our first visit to Destin. The beach is amazing! If we come back we will definitely stay at the Chill Pill! Keep up the good work!
Stayed: March 2023 Submitted: March 15, 2023
Therese H.Great vacation rental!!!!
We have a large family (15+ people) that has rented over 20 vacation homes in the Destin area. This home ranks in the top 5% of our vacation rentals! The location is in the Crystal Beach area and it right across the road from the beach. The Crystal Beach area is a little less crowded than say the Miramar Beach area (which is where we have typically stayed in the past). We were looking for something that had enough bedrooms for our family, close location to the beach but still have a pool for the little ones, and a large gathering area inside the house where our family could gather to wind down the evenings. The pool table and especially the shuffleboard table made for some very fun evenings. This house captured it all. It was a short walk to the beach and we had a private beach which was nice. This is also located next to Henderson State Beach Park. Take a short walk down the beach and it feels like you are the only person on the beach once you get in the Henderson State Beach Park. It is so beautiful and relaxing!! On top of all of this, the price was right and was located in a quaint little neighborhood with white picket fences and very quiet! Additionally, I can't say enough about Dana Flynn (property owner and renter). She was so easy to work with and was so accommodating. If you are looking for a vacation home to rent in the Destin area, this is the house you should be looking into.
Stayed: October 2022 Submitted: October 23, 2022
Host response
"Thanks for your kind words Hollis group! The gathering areas of this house make room for everyone! Come back anytime."
Chris B.Ideal house for multiple families (20+ people)
This house could not be more perfect for 4 - 6 families with kids. Location to the beach is perfect (3 minute walk), large great room with plenty of options for eating/television watching/games and all finishes are the highest quality. House is 5 minutes away from grocery, dozens of restaurants and anything else needed. Dana couldn't be more helpful as well with advice for local amenities.1,000% would stay at this location again.
Stayed: March 2022 Submitted: March 30, 2022
Host response
"So glad your group enjoyed time together at Chill Pill! Thanks for staying with us and come back anytime. Dana"
David T.Sibling long weekend getaway
Very pleased with the Chill Pill property. close to beach access, bikes, beach supplies, 90 degree pool, game room, cleanliness, and interior appointments all really nice. Great big house for everyone to have space. My 4 siblings and their spouses had only positive remarks and comments during the entire weekend on my selection of this property. 5 couples, 5 nights, each cooking a different night with plenty of room and kitchen supplies. Destin and Chill Pill excelled on all levels.
Stayed: February 2022 Submitted: February 27, 2022
Maureen M.Wonderful
The house, amenities and area were amazing! We had family of all ages staying and there was something for all of us to enjoy. The heated pool was awesome! Plenty of room; large kitchen and living area. My husband recently had hip surgery so we had the ground floor master which worked out great! We look forward to returning!
Stayed: December 2021 Submitted: December 17, 2021
Stacy K.Wonderful Experience
We really enjoyed our stay. The home is beautifully appointed and well maintained with alot of extra beach toys and supplies for the sand. I loved having chair service on the beach and the table games at the house. Dana is a dream host and is available if needed. I will stay at her properties in the future.
Stayed: August 2021 Submitted: September 13, 2021
John C.Great House, better than advertised!
It is very difficult to find a home that has: 1. perfect location to the beach 2. perfect location to golf courses 3. has that many bedrooms with en suite bathrooms 4. perfectly kept 5. responsive ownerWill stay there again
Stayed: March 2021 Submitted: March 11, 2021
Colleen M.Beautiful well kept home
A beautify and spacious home with everything we wanted for our family. Everyone had their own room and bathroom. With the nearby beach, a pool, pool table and shuffleboard, we are entertained 24/7. I have already referred friends to stay here. Everything you need is very nearby.
Stayed: February 2021 Submitted: March 05, 2021
Scott M.Best Vacation House Ever!!
My buddies and I used this house for our annual golf trip. Everyone in our group decided that we will come back to this house every year from now on. Dana was a pleasure to work with. Plenty of space for all the guys and everyone had their own bathroom. TVs in every room and the sono system was a plus. If you are traveling with a larger group, this is definitely the place to stay.
Stayed: November 2020 Submitted: November 13, 2020
Host response
"Scott and the Gang - spot on, this is the perfect group house and everyone loves not having to share a bathroom. Glad y'all enjoyed your time and come see us again! Thanks for staying with us and for your kind words. Makes my day! Dana"
Melissa C.Beautiful Home, Great Location, Amazing Property Manager
Where do I begin...this home was not only spacious and filled with all the amenities you would need for your stay but also in a great location. The home is beautiful and the property manager was accommodating and professional. She made sure the home was spotless for us especially during these unprecedented times. The house was stocked with disinfectant and added cleaning supplies. The kitchen utensils were fabulous such as her knives etc. We cooked the whole time we were there and had an amazing time. Her shed outside was filled with paddle boards, rafts, umbrellas, boogie boards etc. The house came with a ton of beach towels and the laundry room had 2 washers 2 dryers and house had two refrigerators. Each bedroom was spacious and cozy. The pool table and shuffle board was so fun. The pool being out back next to old hwy 98 gave for great people watching in the evenings and the bike and walking path was conveniently located in the same area as the pool. Our trip was amazing. Thanks again Dana for sharing your beautiful home with our family.
Stayed: May 2020 Submitted: June 03, 2020
150 steps to our beach access where we provide FREE chair service for six; you'll have bathrooms, shower, trash cans, and be just across the street from Camille's for drinks and lunch.
> free professional chair service for 6
>a stand-up-paddleboard (SUP)
>sea kayak with paddle and life jacket
>rolling beach cart
>6 more folding sand chairs
>3 rolling coolers
>appx 12 beach towels
> a pack-n-play
Within walking distance (15 minutes or less) you have the Destin Commons with dozens of shops, dozens of restaurants like Uncle Bucks with bowling, movie theater, Bass Pro Shop, Starbucks, Panera, Chipotle, Zoe's, Pizza places, drug and grocery stores, and anything else you need. Also two restaurants just a half-block from us (Camille's and 790 on the Gulf).
Member since 2019
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